George Willison, an Edinburgh artist, studied under Anton Raphael Mengs (1728-1779) in Rome in the 1760s, moving to London in 1767 where he exhibited at the Society of Artists 1767-1770 and the Royal Academy 1771-72. In 1772 he applied to the East India Company for permission to travel to India, which was granted on 31 December 1772, after which he set out for Madras, arriving in 1774. There, Willison soon established a reputation as a portraitist, sending portraits of his chief patron, the Nawab of Arcot, to the Society of Artists of Great Britain in 1777 and 1778. He returned to London in 1780, and retired to Edinburgh in c.1784.
Around 1776, Willison was commissioned to paint the portrait of the present sitter, Eyles Irwin, who had travelled to India at the age of seventeen in 1768, and was appointed 'Superintendent of the Company's grounds within the bounds of Madras, Chepak and San Thome'. Mildred Archer (op. cit., p.106) notes that Willison's portrait of Irwin, a supporter in the scandal surrounding the removal of Lord Pigot from his office as Governor of Madras in 1776, shows significant similarities to Willison's portrait of Lord Pigot, several versions of which the artist painted around the same time: 'According to family tradition, Willison executed a sensitive portrait of [Irwin], employing the same oval format as in the Pigot picture. It is significant that in both portraits rucks in the sleeves of the garments worn by the sitters are executed in the same brusquely simplified manner'. Irwin was temporarily suspended from service at this time, but was re-instated in 1777, and was 'later to have a brilliant career under Lord Macartney, Governor of Madras, displaying...a character remarkable for its amiable simplicity' (Mildred Archer, ibid.).